Methylamine → 3-(Aminomethyl)-5-bromopyridine

HRID 1350109Notes

Reaction equation

HRID 1350109 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2C(=O)C3=CC=CC=C3C2=O)[CH:5]=[N:6][CH:7]=1.CN.[OH-].[Na+]>Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH2:9])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 229922612-((5-Bromopyridin-3-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 229922643-(Aminomethyl)-5-bromopyridineYield 59.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-Bromo-3-(phthalimidomethyl)pyridine (7.9 g, 25 mmol) is then hydrolyzed by treatment with aqueous methylamine (40%, 50 mL) and refluxing the mixture for 3 h. The solvents were removed by rotary evaporation to yield a pale yellow-colored solid, which was then taken up into concentrated hydrochloric acid (50 mL) and refluxed for 15 h. The reaction mixture was basified (pH=10–11) with aqueous sodium hydroxide (50%), extracted with chloroform (5×40 mL) and dried (K2CO3). The solvent was removed by rotary evaporation and the product purified by column chromatography to yield (5-bromo-3-pyridyl)methylamine (2.80 g, 59.8% yield).

Workup

  1. customThe solvents were removed by rotary evaporation
  2. customto yield a pale yellow-colored solid, which
  3. temperaturerefluxed for 15 h
  4. extractionextracted with chloroform (5×40 mL)
  5. dry with materialdried (K2CO3)
  6. customThe solvent was removed by rotary evaporation
  7. customthe product purified by column chromatography

Sources & evidence

ORD record
ord-d8965984300644c7a235b7633ae65704
Source dataset
uspto-grants-2007_05
Patent number
US07214686B2

Reaction notes

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